Nantucket, Massachusetts

If you're anywhere in the Northeast, and you want to experience the best vacation the region has to offer, you need to keep Nantucket high on your list of options. The location of summer homes belonging to everyone from Bill Belichick to Tommy Hilfiger, this island, whose Wampanoag Indian name translates as "Place of Peace," has long been a premium spot for maxing and relaxing. Take a stroll by Sayle's Seafood for a fresh-caught bite, and then head to the Chicken Box for a little local nightlife.